Acetic Acid → N2-(1-(quinolin-2-yl)azetidin-3-yl)pyridine-2,3-diamine

HRID 707344ノート

反応式

HRID 707344 の反応式
[N+:1]([C:4]1[C:5]([NH:10][CH:11]2[CH2:14][N:13]([C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]=3)[CH2:12]2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.C(O)(=O)C>C(O)C.O.[Fe]>[N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:15]=1[N:13]1[CH2:14][CH:11]([NH:10][C:5]2[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][N:6]=2)[CH2:12]1

参加物

6

反応物 2

HCID 176Acetic AcidHCID 866942023-nitro-N-(1-(quinolin-2-yl)azetidin-3-yl)pyridin-2-amine

生成物 1

HCID 86694203N2-(1-(quinolin-2-yl)azetidin-3-yl)pyridine-2,3-diamine収率 81.2%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
95 °C

実験手順

To a solution of 3-nitro-N-(1-(quinolin-2-yl)azetidin-3-yl)pyridin-2-amine (1.05 g, 3.20 mmol) in ethanol (30 mL) and water (10 mL) was added iron (448 mg, 8.0 mmol) and acetic acid (240 mg, 4.0 mmol) slowly dropwise. The mixture was heated at 95° C. until TLC analysis confirmed the absence of starting materials. The reaction mixture was filtered through a plug of CELITE™ washing with methanol. The black filtrate was concentrated in vacuo, treated with brine (40 mL) and extracted with dichloromethane (3×60 mL). The combined organic extracts were washed with water (30 mL) and brine (30 mL) and then dried over sodium sulfate. The filtrate was evaporated in vacuo to give N2-(1-(quinolin-2-yl)azetidin-3-yl)pyridine-2,3-diamine (0.744 g, 2.6 mmol, yield 80%).

後処理

  1. filtrationThe reaction mixture was filtered through a plug of CELITE™
  2. washwashing with methanol
  3. concentrationThe black filtrate was concentrated in vacuo
  4. additiontreated with brine (40 mL)
  5. extractionextracted with dichloromethane (3×60 mL)
  6. washThe combined organic extracts were washed with water (30 mL) and brine (30 mL)
  7. dry with materialdried over sodium sulfate
  8. customThe filtrate was evaporated in vacuo

出典と根拠

ORDレコード
ord-b28e388cbf574c348ff6dcbf723cd7b0
出典データセット
uspto-grants-2015_11
特許番号
US09174992B2

反応ノート

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